For nearly three decades, Bill Gurley has been one of the most influential voices in Silicon Valley \u2014 a general partner at Benchmark whose early bets on companies like Uber, Zillow, and Stitch Fix helped define what modern venture capital looks like. Now, having moved to Austin and stepped back from active investing, the native Texan is channeling that same pattern-recognition instinct into something different: a book, a foundation, and a policy institute aimed at problems he thinks he can actually help solve.<\/p>\n
The book is \u201cRunnin\u2019 Down a Dream\u201d \u2014 a nod to Tom Petty and also an argument that following your passion isn\u2019t just romanticized career advice but a true competitive strategy, one that becomes only more urgent as AI rapidly reshapes the workforce. The foundation, which he\u2019s calling the Running Down a Dream Foundation, will award 100 grants of $5,000 a year to people who need a financial cushion to make a leap they\u2019ve been afraid to take.<\/p>\n
We caught up with Gurley to talk about all of it \u2014 including what he makes of the somewhat surreal reality that several of his former peers in tech now hold enormous sway in Washington, why he thinks the 996 grind culture many young founders have adopted is less alarming than it sounds, and what AI really means for your career. The following has been edited for length and clarity. Our full conversation with Gurley drops Tuesday on TC\u2019s StrictlyVC Download podcast.<\/p>\n
Why write this book?<\/p>\n
I went through a phase where I was reading a lot of biographies \u2014 people from very different fields, different time windows \u2014 and I started noticing patterns the way I would notice patterns in a market evolving. I wrote them down. A couple years later I got invited to speak at the University of Texas, dusted off the notes, built a presentation. They posted it on YouTube, and James Clear \u2014 who wrote \u201cAtomic Habits\u201d \u2014 noticed and posted about it. That\u2019s what got me thinking about a book. And when I went through my own process of moving away from venture and thinking about what I wanted to do next, it became obvious I didn\u2019t want to write about VC or Uber or any of that. I wanted to do something that could have a bigger mission.<\/p>\n
Your research with Wharton found that roughly 60% of people would do things differently if they could start their careers over. That shocked you. Why?<\/p>\n
When we first ran it as a SurveyMonkey poll we got seven out of 10. When we did it more rigorously with Wharton, we got six out of 10. One of the things that strikes me is that we have a phrase in the book \u2014 life is a use it or lose it proposition \u2014 and when you\u2019re young, it\u2019s just hard to have that framing. It\u2019s hard to fast-forward through all of your time and recognize how precious it is. Daniel Pink has done a lot of work on what he calls regrets of inaction \u2014 the thing that weighs on people most as they get older is the thing they didn\u2019t try, the stone left unturned. That holds across multiple geographies and cultures. And I think a lot of well-intentioned parents feel more responsibility to create economic stability for their kids than to encourage them to truly explore their passion. Especially with AI out there, that may not have been the right call.<\/p>\n
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Exploring your passion sounds like easier advice for people who have financial runway. What do you say to someone working paycheck to paycheck?<\/p>\n
A few things. First, the book profiles people who started on the very bottom rung and climbed to the top \u2014 [celebrity hairstylist and entrepreneur] Jen Atkins moved to LA with $200 in her pocket. There\u2019s nothing in the book that says you need to start anywhere other than right at the beginning. Second, if you\u2019re living paycheck to paycheck, I wouldn\u2019t encourage you to quit. I\u2019d encourage you to use your free time to build a little document on your phone about what your thing might be. Learn. Prepare to jump before you jump. And third \u2014 this is why I\u2019m launching the foundation. The last page of the book talks about it: We\u2019re going to give 100 grants a year of $5,000 to people who are in exactly that position, who can convince us in an application that they\u2019ve thought long and hard about where they want to go but need a little help getting there.<\/p>\n
You\u2019ve been outspoken for years about regulatory capture \u2014 the idea that big companies use regulation to entrench themselves.<\/p>\n
I gave a speech on regulatory capture a few years back \u2014 it was at the All-In Summit \u2014 and at the time I said I had a fear that the AI companies would try to use regulation to protect themselves. I think that\u2019s happening now. The flip side is that there are legitimate questions: Jonathan Haidt\u2019s book \u201cAnxious Generation\u201d has been on the bestseller list for almost two years, arguing social media has been really bad for children, with academic research to back it up. People would say we should have gotten in front of social media and need to do it with AI. The problem is that the people begging for regulation the most in AI are the actual companies themselves, and that makes me skeptical. There\u2019s also the global dimension \u2014 if U.S. AI gets entangled in state-by-state regulation and Chinese models are running free, we\u2019re going to paint ourselves in red tape. I always ask people: What are your favorite five regulations of all time, and how were they successful? Do you have any confidence that people at the state level in a random state know how to write good AI regulation that will actually work?<\/p>\n
It\u2019s a little surreal that several prominent figures from your world now hold enormous influence in Washington. What do you make of that?<\/p>\n
It\u2019s very ironic. If you go back and watch that regulatory capture talk, who would have thought a few years later David Sacks would actually be [special advisor for AI and crypto in the White House]?<\/p>\n
Back in 2018, Mike Moritz of Sequoia wrote in the FT that Americans would lose to China if they didn\u2019t start working harder. It was controversial at the time, but a lot of young founders here seem to have since embraced a punishing work culture \u2014 the 996 ethos. What are your thoughts about what\u2019s happening?<\/p>\n
I kind of love it, honestly. I think Silicon Valley got really lazy during COVID \u2014 people weren\u2019t coming into the office, the culture got soft in a way I hadn\u2019t seen in all my years there. And I\u2019ve been to China six times. I know what Michael Moritz was describing when he said we\u2019re going to lose not because they\u2019re smarter but because they have a better work ethic. But here\u2019s the thing: If you study successful people across a lot of fields, we think it\u2019s wonderful when an athlete practices 12 hours a day or when an artist works obsessively on their craft. Nobody says Jordan didn\u2019t have work-life balance. We just don\u2019t extend the same logic to building a company. If those founders love what they\u2019re doing that much, and they feel like this is the moment to go hard, that\u2019s actually precisely the point of the book: Find the thing that makes you feel that way.<\/p>\n
You talk about mentorship in the book. What makes a great mentor relationship and how do people find one?<\/p>\n
The number one thing is to get out of your head this idea that gets passed around in the self-help world: \u201cgo get a mentor,\u201d and everyone runs out and cold calls someone that\u2019s ridiculously too high and unachievable, and it doesn\u2019t work. For all those people who are really out of reach right now, I call them aspirational mentors \u2014 create a persona of them, just like I was talking about with the dream job folder. Get clips of all the books they\u2019ve written, podcasts they\u2019ve done, interviews they\u2019ve done, and study them. You can learn a lot from people without talking to them directly, especially in the modern age. And then for your real mentors, go two levels down from where you thought you were going to aim. Discover somebody \u2014 tools like LinkedIn make this so easy \u2014 and be the first person to ever call them and ask them to be a mentor, because they\u2019ll be flattered. They\u2019ll be flattered that you knew who they were. Imagine anyone getting their first call to be a mentor. It\u2019s a great feeling. You\u2019re going to have way more success with that interaction than shooting too high.<\/p>\n
I\u2019ll tell you a funny story: I started getting so many calls from people who wanted to break into venture that I wrote a three-page PDF called \u201cSo You Want to Be a VC,\u201d and hidden in the third page was basically \u2014 go do X, go do Y, go do Z, come back and tell me how that went. The number of people that actually ended up talking to me after getting that document was a fraction of the number I sent it to. It\u2019s funny how much it thinned when you gave them a little homework to do.<\/p>\n
You started working on this book before the impacts of AI became clearer. Does that at all change how people should think about their careers?<\/p>\n
If you\u2019re following the traditional path \u2014 going through the career center at your university, signing up on a list, waiting for a recruiter to sit through 30 people in 20-minute slots \u2014 you look like a cog. You look mass-produced. For that group, AI looks frightening, and maybe it should. But if you are blazing your own trail, using the techniques in the book, becoming what I call a candidate of one \u2014 someone whose path looks completely unique because you\u2019ve built it intentionally \u2014 then every tool in this book is amplified by AI. Learning has never been easier than right now, in the entire history of the world. If you\u2019re running toward it, if you\u2019re becoming the most AI-aware person in your field, this thing is nothing but a superpower.<\/p>\n
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